Structural identification of organic compounds with spectroscopic techniques:
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| Language: | English |
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2005
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| Item Description: | Aus dem Chines. übers. |
| Physical Description: | XVI, 452 S. Ill., graph. Darst. |
| ISBN: | 3527312404 |
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| 100 | 1 | |a Ning, Yong-Cheng |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Structural identification of organic compounds with spectroscopic techniques |c Yong-Cheng Ning |
| 264 | 1 | |a Weinheim |b WILEY-VCH |c 2005 | |
| 300 | |a XVI, 452 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Aus dem Chines. übers. | ||
| 650 | 4 | |a Análisis espectral | |
| 650 | 7 | |a Organische verbindingen |2 gtt | |
| 650 | 7 | |a Spectrometrie |2 gtt | |
| 650 | 4 | |a Organic compounds |x Structure |x Analysis | |
| 650 | 4 | |a Spectrum analysis | |
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| adam_text | IX
Contents
Foreword
V
Prefece VI!
1
Introduction to Nuclear Magnetic Resonance I
1.1
Basic Principle of NMR
í
1.1.1
Nuclear Magnetic Momentum
1
1.1.2
Quantization of Angular Momentum and Magnetic Moment
3
1.1.3
Nuclear Magnetic Resonance
4
1.2
Chemical Shift
6
1.2.1
Shielding Constant
6
1.2.2
Chemical Shift
ό
7
1.3
Spin-spin Coupling
8
1.3.1
Spin-spin Coupling Produces NMR Signal Splitting
8
1.3.2
Energy Level Diagram
9
1.3.3
Coupling Constant
] 10
1.4
Magnetization
11
1.4.1
Magnetization Concept
11
1.4.2
Rotating Frame
12
1.5
Relaxation Process
14
1.5.1
What is a Relaxation Process?
14
1.5.2
Longitudinal and Transverse Relaxation
15
1.5.3
Width of an NMR Signal
17
1.6
Pulse-Fourier Transform NMR Spectrometer
18
1.6.1
Application of Strong and Short RF Pulses
18
1.6.2
Time Domain Signal and Frequency Domain Spectrum,
and their Fourier Transform
20
1.6.3
FT-NMR with Respect to the Fourier Decomposition
22
1.6.4
Advantages of an FT-NMR Spectrometer
24
1.7
Recent Developments in NMR Spectroscopy
25
1.8
References
26
Χ ι
Contents
2
^И
N
MR Spectroscopy
27
2.1
Chemical Shift
28
2.1.1
Reference for Chemical Shift
28
2.1.2
Factors Affecting Chemical Shifts
28
2.1.3
Chemical Shift Values of Common Functional Groups
34
2.2
Coupling Constant
J
38
2.2.1
Vector Model for Couplings
38
2.2.2
V and 2J
39
2.2.3
3y
40
2.2.4
Coupling Constants of Long-range Couplings
43
2.2.5
Couplings in a Phenyl Ring or in a Heteroaromatic Ring
43
2.3
Spin-spin Coupling System and Classification of NMR Spectra
45
2.3.1
Chemical Equivalence
45
2.3.2
Magnetic Equivalence
49
2.3.3
Spin System
50
2.3.4
Classification of NMR Spectra
51
2.4
Common Second-order Spectra
52
2.4.1 AB
System
52
2.4.2 AB 2
System
54
2.4.3
AMX System
55
2.4.4
ABX System
55
2.4.5
AA BB System
57
2.5
Spectra of Common Functional Groups
57
2.5.1
Substituted Phenyl Ring
57
2.5.2
Substituted Heteroaromatic Ring
60
2.5.3
Mono-substituted
Ethylene
60
2.5.4
Normal Long-chain
Alkyl
60
2.6
Methods for Assisting the Spectrum Analysis
61
2.6.1
Using a Spectrometer with a High Frequency
61
2.6.2
Deuterium Exchange
61
2.6.3
Medium Effect
62
2.6.4
Shift Reagents
62
2.6.5
Spectral Simulation by Computer
62
2.7
Double Resonance
62
2.7.1
Spin Decoupling
63
2.7.2
Nuclear Overhauser Effect
67
2.8
Dynamic Nuclear Magnetic Resonance
70
2.8.1
Description of Dynamic Nuclear Magnetic Resonance
70
2.8.2
Spectral Peak of Reactive Hydrogen Atom (OH, NH and SH)
72
2.9
Interpreting
гН
NMR
Spectra
74
2.9.1
Sampling and Measurement
75
2.9.2
Steps for
H
Spectrum Interpretation
75
2.9.3
Examples of 1
H
Spectrum Interpretation
78
2.10
References
89
Contents
І
XI
3
С
NMR Spectroscopy
91
3.1
Introduction
91
3.1.1
Advantages of 13C NMR Spectra
91
3.1.2
Difficulties in the Measurement of C NMR Spectra
92
3.1.3
I3C NMR Spectra
92
3.2
Chemical Shift
92
3.2.1
Paramagnetic Shielding is the Decisive Factor for Chemical
Shifts
93
3.2.2
Alkanes and their Derivatives
93
3.2.3
Cycloalkanes and their Derivatives
95
3.2.4
Alkenes and their Derivatives
96
3.2.5
Benzene and its Derivatives
97
3.2.6
Carbonyl Compounds
99
3.2.7
Influences of Hydrogen Bonds and the Medium
101
3.3
Coupling and Decoupling Methods in 13C Spectra
201
3.3.1
Coupling in 13C Spectra
101
3.3.2
Broadband Decoupling
102
3.3.3
Off-resonance Decoupling
104
3.3.4
Selective Decoupling
104
3.3.5
Gated Decoupling
104
3.4
Relaxation
105
3.4.1
Why does the Discussion of Relaxation of 13C Nuclei Require a
Whole Section?
205
3.4.2
Basic Concepts of the Relaxation of 13C Nuclei
205
3.4.3
Measurement of Relaxation Time
206
3.4.4
Application of
Тг
109
3.5
Interpretation of 13C NMR Spectra
120
3.5.1
Sampling and Plotting
2 20
3.5.2
Steps for the Interpretation of 13C Spectra
222
3.5.3
Examples of the Interpretation of 13C Spectra
223
3.6
References
226
4
Application of Pulse Sequences and Two-dimensional NMR
Spectroscopy
227
4.1
Fundamentals
127
4.1.1
Transverse Magnetization Vector
227
4.1.2
Coherence and Related Topics
130
4.1.3
Spin Echo
232
4.1.4
The Phase of an NMR Signal is Modulated by the Chemical
Shift
236
4.1.5
Bilinear Rotational Decoupling, BIRD
237
4.1.6
Spin Locking
238
4.1.7 Isotropie
Mixing
242
XII Contents
4.1.8
Selective
Population Inversion 143
4.1.9 Pulsed-field Gradient 147
4.1.10
Shaped
Pulse 152
4.2
Spectrum Editing
154
4.2.1
J
Modulation
or APT
154
4.2.2
INEPT (Insensitive Nuclei Enhancement by Polarization
Transfer)
157
4.2.3
DEPT
(Distortionless Enhancement by Polarization Transfer)
160
4.3
Introduction to 2D NMR
162
4.3.1
What are 2D NMR Spectra?
362
4.3.2
Time Axis of 2D NMR
163
4.3.3
Classification of 2D NMR Spectra
164
4.3.4
Illustration of 2D NMR Spectra
364
4.4
J
Resolved Spectra
365
4.4.1
Homonuclear
J
Resolved Spectra
365
4.4.2
Heteronuclear
J
Resolved Spectra
368
4.5
Heteronuclear Shift Correlation Spectroscopy
369
4.5.1
H,C-COSY
369
4.5.2
CO
LOC
172
4.5.3
Η,Χ
-COSY
373
4.6
Homonuclear Shift Correlation Spectroscopy
174
4.6.1
COSY
375
4.6.2
Phase-sensitive Homonuclear Shift Correlation Spectroscopy
378
4.6.3
COSY-45
(jß-COSY) 182
4.6.4
COSY with Decoupling on the <ox Axis
183
4.6.5
COSYLR
384
4.6.6
DQF-COSY
386
4.7
NOESY and its Variations
187
АЛЛ
NOESY
188
4.7.2
ROESY
389
4.7.3
HOESY
393
4.8
Relayed Correlation Spectra and Total Correlation Spectra
192
4.8.1
RCOSY
192
4.8.2
Heteronuclear Relayed COSY
393
4.8.3
Total Correlation Spectroscopy (TOCSY)
395
4.9
Multiple Quantum 2D NMR Spectra
398
4.9.1
2D INADEQUATE
398
4.9.2
Two-dimensional Double Quantum Spectra of1
H
201
4.10
Ή
Detected Heteronuclear Correlation Spectra
202
4.10.1
HMQC and HSQC
203
4.10.2
HMBC
206
4.11
Combined 2D NMR Spectra
208
4.12
Three-dimensional NMR Spectra
209
4.12.1
Principle of Three-dimensional NMR Spectra
209
4.12.2
Classification of
3D
NMR Spectra
230
Contents Xlii
4.12.3 Application
of
3D NMR
Spectra
210
4.13 DOSY 211
4.14
References
213
5
Organic Mass Spectrometry
215
5.1
Fundamentals of Organic Mass Spectrometry
216
5.1.1
Instruments
216
5.1.2
Major Specifications
226
5.1.3
Mass Spectrum
217
5.1.4
Ion Types in Organic Mass Spectrometry
227
5.2
Mass Analyzers
229
5.2.1
Single-focusing or Double-focusing Mass Analyzers
229
5.2.2
Quadrupole Mass Analyzers
222
5.2.3
Ion Trap
223
5.2.4
Fourier Transform Mass Spectrometer
228
5.2.5
Time-of-flight
(TOF)
MS
232
5.3
lonization
233
5.3.1
Electron Impact lonization, El
233
5.3.2
Chemical lonization,
CI
234
5.3.3
Field lonization and Field Desorption
235
5.3.4
Fast Atom Bombardment, FAB, and Liquid Secondary Ion Mass
Spectrometry, LSIMS
236
5.3.5
Matrix-assisted Laser Desorption-ionization, MALDI
236
5.3.6
Atmospheric Pressure lonization, API
237
5.4
Metastable Ions and their Measurement
238
5.4.1
Metastable Ions Produced in the Second Field-free Region
240
5.4.2
Metastable Ions Produced in the First Field-free Region
242
5.4.3
Ion Kinetic Energy Spectrum (IKES)
242
5.4.4
Mass-analyzed Ion Kinetic Energy Spectrum (MIKES)
242
5.4.5
Linked Scanning
242
5.4.6
Information Provided by Metastable Ions
245
5.4.7
Peak Shapes of Metastable Ions
246
5.5
Tandem Mass Spectrometry (MS )
246
5.5.1
Collision-induced Dissociation
(CID)
246
5.5.2
Tandem Mass Spectrometry
248
5.6
Combination of Chromatography and Mass Spectrometry
252
5.6.1
GC-MS
252
5.6.2
LC-MS and LC-MS
253
5.7
References
254
6
Interpretation of Mass Spectra
257
6.1
Determination of Molecular Weight and Elemental
Composition
257
6.1.1
Determination of Molecular Weight by an El Spectrum
257
XIV
I Contents
6.1.2
Determination of the Molecular Weight from a Multiply-charged Ion
Cluster in an ESI Spectrum
259
6.1.3
Postulation
of the Molecular Weight from a Spectrum Obtained
Using Soft Ionization Techniques
261
6.1.4
Determination of the Molecular Formula from High Resolution
MS Data
261
6.1.5
Peak Matching
262
6.1.6
Postulation
of the Molecular Weight from Low Resolution
MS Data
262
6.1.7
Measurement of Exact Masses by a TOF or Quadrupole
265
6.2
Reactions and their Mechanisms in Organic Mass
Spectrometry
265
6.2.1
Basic Knowledge
265
6.2.2
Simple Cleavage
266
6.2.3
Rearrangements
273
6.2.4
Cleavage of Alicyclic Compounds
279
6.2.5
Consecutive Decompositions of Primary Fragmentation Ions
281
6.2.6
Stevenson-Audieťs
Rule
281
6.2.7
Methods to Study Reaction Mechanisms of Organic Mass
Spectrometry
283
6.3
Mass Spectrum Patterns of Common Functional Groups
284
6.3.1
Alkanes
284
6.3.2
Unsaturated Hydrocarbons
286
6.3.3
Aliphatic Compounds Containing Saturated
Heteroatoms
287
6.3.4
Aliphatic Compounds Containing Unsaturated
Heteroatoms
290
6.3.5
Alkyl
Benzenes
291
6.3.6
Aromatic Compounds with
Heteroatom
Substitutions
292
6.3.7
Heteroaromatic Compounds and their Derivatives
293
6.4
Interpretation of Mass Spectra
293
6.4.1
Steps of the Interpretation
294
6.4.2
Examples
295
6.5
Library Retrieval of Mass Spectra
305
6.6
Interpretation of the Mass Spectra from Soft Ionization
310
6.6.1
Mass Spectra from
CI
310
6.6.2
Mass Spectra from FAB
311
6.6.3
Mass Spectra from MALDI
312
6.6.4
Mass Spectra from ESI
313
6.6.5
Mass Spectra from APCI
314
6.7
References
314
7
Infrared Spectroscopy and Raman Spectroscope
315
7.1
General Information on Infrared Spectroscopy
315
7.1.1
Wavelength and Wavenumber
315
7.1.2
Near, Medium and Far Infrared Rays
316
7.1.3
The
Ordinate
of
IR
Spectra
316
Contents
XV
7.2
Basic Theory of
IR Spectroscopy
316
7.2.1
IR
Absorption Frequencies of a Diatomic Molecule
336
7.2.2
IR
Absorption Frequencies of a Polyatomic Molecule
320
7.2.3
IR
Absorption Intensities
322
7.3
Characteristic Frequencies of Functional Groups
322
7.3.1
Functional Groups Possessing Characteristic Frequencies
322
7.3.2
Factors Affecting Absorption Frequencies
323
7.3.3
Characteristic Frequencies of Common Functional Groups
324
7.4
Interpretation of
IR
Spectra
325
7.4.1
Wavenumber Regions of
IR
Absorption Bands
325
7.4.2
Fingerprint and Functional Group Regions
327
7.4.3
Key Points for the Interpretation of
IR
Spectra
328
7.4.4
Examples of
IR
Spectrum Interpretation
329
7.5
Recent Developments in Infrared Spectroscopy
334
7.5.1
Step Scan
334
7.5.2
Photo-acoustic Spectroscopy
337
7.5.3
Time-resolved Spectroscopy
339
7.5.4
Two-dimensional Infrared Spectroscopy
340
7.5.5
Infrared Microscope and Chemical Imaging
343
7.5.6
GC-FT-IR
344
7.6
Principle and Application of Raman Spectroscopy
346
7.6.1
Principle of Raman Spectroscopy
346
7.6.2
Advantages and Applications of Raman Spectroscopy
350
7.6.3
FT Raman Spectrometer
352
7.7
References
354
8
Identification of an Unknown Compound through a Combination
of Spectra
355
8.1
Structural Identification of an Unknown Compound
by Combination of One-dimensional NMR and Other Spectra
356
8.2
Determination of the Functional Groups (or Structural Units)
of an Unknown Compound
358
8.2.1
Substituted Benzene Ring
359
8.2.2
Normal Long-chain
Alkyl
Groups
360
8.2.3
Alcohols and Phenols
360
8.2.4
Carbonyl Compounds
363
8.3
Deduction of the Structure of an Organic Compound on the Basis
of2D NMR Spectra
363
8.3.1
Shift Correlation Spectra as the Key to Structural
Postulation
363
8.3.2
Deduction of the Structure of an Unknown Compound by Using
Mainly HMQC-TOCSY
366
8.3.3
Postulating an Unknown Structure by 2D INADEQUATE
368
8.4
Examples of Structural Identification or Assignment
369
8.5
References
398
XV!
Contents
9 Determination
of
Configuration
and Conformation
of Organic Compounds by
Spectroscopie
Methods
399
9.1
NMR
400
9.1.1
Chemical Shift
400
9.1.2
Coupling Constants
407
9.1.3
NOE
414
9.2
Mass Spectrometry
417
9.2.1
Utilizing Electron Impact Ionization
418
9.2.2
Utilizing Soft Ionization
420
9.2.3
Reaction Mass Spectrometry
421
9.3
Infrared and Raman Spectroscopy
422
9.4
References
425
Appendix
1
Product Operator Formalism for Pulse Sequences
427
Appendix
2
Characteristic Frequencies of Common Functional Croups
437
Index
449
Velearly
structured, easy to read and optimal to understand, this exten¬
sive compendium fills the gap between those textbooks devoted to either
spectra interpretation or basic physical principles. All the material has
been gathered from the latest literature from around the world, with
additional technical information provided by the manufacturers of
spec¬
troscopie
instruments.
Alongside basic methods, Professor
Ning
presents up-to-date devel¬
opments in NMR, MS,
IR
and Raman spectroscopy, such as pulsed-field
gradient technique, LC-NMR, and DOSY. He stresses the application
of
spectroscopie
methods, interpreting them in great detail and depth
since most of the selected spectra may be applied to practical work, as
well as summarizing the rules for their interpretation. He also incorpo¬
rates his original ideas, including a comparison of the common points
in different
spectroscopie
techniques.
Following an introductory chapter on the basic principles of NMR,
featuring two complementary discussions on the pulsed Fourier trans¬
form NMR spectrometer, there follow three chapters on
Ή
NMR,
C NMR, and two-dimensional NMR spectroscopy. Subsequent chap¬
ters are devoted to organic mass spectrometry and the interpretation of
mass spectra, infrared and Raman spectroscopy, as well as the combina¬
tion of NMR, MS, and
IR
spectra to find a structure. The last chapter
is devoted to the determination of configuration and conformation by
spectroscopie
methods.
Yong-Cheng
Ning
studied at the Engineering-Physics Depart¬
ment ofTsinghua University, Beijing, China where after his
graduation he worked as a faculty member. From igji to igyS
he researched on structural identification of organic compounds
at the Institute of Chemical Engineering in Shenyang. Between
ідбі
and
1984
Yong-Cheng
Ning
participated in researches in
the NMR, MS, X-ray diffraction and alkaloid laboratories of
the Institute of Chemistry of Natural Substances in Paris. Since
1993
he is a full professor at Tsinghua University. Yong-Cheng
Ning s books won several awards, e.g., the prize for excellent
teaching materials, with this book recommended as a textbook
for Chinese graduate students by the Ministry of Education of
China.
|
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| dewey-full | 543.5 |
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| dewey-ones | 543 - Analytical chemistry |
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| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV019753628 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T20:05:21Z |
| institution | BVB |
| isbn | 3527312404 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-013080127 |
| oclc_num | 58970192 |
| open_access_boolean | |
| owner | DE-M49 DE-BY-TUM DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-20 DE-703 DE-634 DE-11 DE-355 DE-BY-UBR |
| owner_facet | DE-M49 DE-BY-TUM DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-20 DE-703 DE-634 DE-11 DE-355 DE-BY-UBR |
| physical | XVI, 452 S. Ill., graph. Darst. |
| publishDate | 2005 |
| publishDateSearch | 2005 |
| publishDateSort | 2005 |
| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Ning, Yong-Cheng Verfasser aut Structural identification of organic compounds with spectroscopic techniques Yong-Cheng Ning Weinheim WILEY-VCH 2005 XVI, 452 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Aus dem Chines. übers. Análisis espectral Organische verbindingen gtt Spectrometrie gtt Organic compounds Structure Analysis Spectrum analysis Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Strukturaufklärung (DE-588)4183788-5 gnd rswk-swf Spektroskopie (DE-588)4056138-0 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 s Strukturaufklärung (DE-588)4183788-5 s Spektroskopie (DE-588)4056138-0 s DE-604 Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013080127&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013080127&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext |
| spellingShingle | Ning, Yong-Cheng Structural identification of organic compounds with spectroscopic techniques Análisis espectral Organische verbindingen gtt Spectrometrie gtt Organic compounds Structure Analysis Spectrum analysis Organische Verbindungen (DE-588)4043816-8 gnd Strukturaufklärung (DE-588)4183788-5 gnd Spektroskopie (DE-588)4056138-0 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4183788-5 (DE-588)4056138-0 |
| title | Structural identification of organic compounds with spectroscopic techniques |
| title_auth | Structural identification of organic compounds with spectroscopic techniques |
| title_exact_search | Structural identification of organic compounds with spectroscopic techniques |
| title_full | Structural identification of organic compounds with spectroscopic techniques Yong-Cheng Ning |
| title_fullStr | Structural identification of organic compounds with spectroscopic techniques Yong-Cheng Ning |
| title_full_unstemmed | Structural identification of organic compounds with spectroscopic techniques Yong-Cheng Ning |
| title_short | Structural identification of organic compounds with spectroscopic techniques |
| title_sort | structural identification of organic compounds with spectroscopic techniques |
| topic | Análisis espectral Organische verbindingen gtt Spectrometrie gtt Organic compounds Structure Analysis Spectrum analysis Organische Verbindungen (DE-588)4043816-8 gnd Strukturaufklärung (DE-588)4183788-5 gnd Spektroskopie (DE-588)4056138-0 gnd |
| topic_facet | Análisis espectral Organische verbindingen Spectrometrie Organic compounds Structure Analysis Spectrum analysis Organische Verbindungen Strukturaufklärung Spektroskopie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013080127&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=013080127&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT ningyongcheng structuralidentificationoforganiccompoundswithspectroscopictechniques |